Saturday Night Live has been home to over a hundred cast members throughout the past 37 years. In our column Saturday Night’s Children, we present the history, talent, and best sketches of one SNL cast member every other week for your viewing, learning, and laughing pleasure.

Mistakes on live television are inevitable even for the most experienced SNL cast members, but where character breaking and even accidental F-bombs have garnered Lorne Michaels’s forgiveness, Damon Wayans’s firing remains the show’s most infamous case of intentional sketch sabotage. Frustrated with his lack of traction during SNL’s struggling eleventh season, Wayans committed a live TV no-no after he switched a straight-man cop role into a clownish and effeminate sketch derailer without warning. But like several others who couldn't hack the waiting around while their youthful energy waned, film and TV success and fame would soon be his, both solo and with his fellow Wayans brethren.

The third of ten children, Damon’s childhood was at the mercy of his strict and often abusive Jehovah’s Witness parents, whose religious beliefs required the Wayans children to be inside their tiny apartment in Chelsea’s Fulton Housing Projects by 6:00PM every day. Shut in with little more than Batman episodes and each other, the Wayans kids developed an early drive to entertain and vie for attention (every one would go on to become actors, screenwriters, or composers). For Damon the need went beyond sibling competition; born with a clubfoot, he faced constant ridicule by classmates for his orthopedic shoes and leg braces and sometimes channeled his inner anger through after school bouts of petty theft. He dropped out of high school after ninth grade.

After bouncing from one odd job to the next, Damon decided to follow in the footsteps of his older brother Keenan and move to Los Angeles to pursue comedy. He tried standup in 1982 at the age of 22 and played a gay hotel employee in Eddie Murphy’s Beverly Hills Cop two years later. By the time Lorne Michaels returned to produce SNL in 1985, Wayans had been around the country on tour and was hired as a featured player along the all-new season 11 cast.

With the exception of a few one-off impersonations (singers Little Richard and Babyface; Louis Farrakhan), Wayans only landed two recurring characters: one as part of the Seinfeld comics AKA “The Stand-Ups" (with Lovitz and Miller) and as Ned Jones the seedy criminal salesman opposite Hall as his partner-in-crime. He also appeared on Weekend Update as the pimped-out “Uptown Financial Analyst” ("Mo' money, mo' money, mo' money!"), but by his 12th episode his frustrations over feeling held back culminated in a sketch called “Mr. Monopoly” in which he played a bit part as a cop but unexpectedly delivered the lines in the vein of his flamboyant character in Beverly Hills Cop. He explained in Live from New York:

What was I supposed to do? I was supposed to just be a cop. But I was frustrated, because I think Lorne Michaels thought he was protecting me by not putting me out there, letting me do my thing. So I started walking around wearing dark shades. When they asked me what was wrong, I said, “It’s too white in here, it hurts my eyes.” I was really on the verge of a nervous breakdown, or just taking a gun and killing everybody.

According to Michaels, Wayans “broke the big rule” with his impromptu character switch-up. He was fired immediately thereafter but still returned to do a standup set during the May 24th season finale. After appearing in Earth Girls Are Easy (1988), his brother’s films I’m Gonna Git You Sucka (1988) and Hollywood Shuffle (1987), and his first hour-long HBO special Damon Wayans: The Last Stand? in 1990, he returned again alongside his brothers and sister for their new Fox sketch show In Living Color, where he racked up a list of hit characters for three Emmy-nominated seasons including Homey D. Clown, philosophical homeless man Anton Jackson, and another flamboyant character Blaine Edwards, one of two borderline offensive mincing gay film critics with cast mate David Alan Grier.

After In Living Color, Wayans went on to appear in more films, stressing the big budget A-list and raunch this time (The Last Boy Scout, Mo' Money, Major Payne, Bulletproof), star in sitcoms and sketch shows (Fox’s Damon in 1998; ABC’s My Wife and Kids from 2001-2005; Showtime’s The Underground in 2006), produce the short-lived semi-biographical WB cartoon series Waynehead as well as the Fox drama series 413 Hope St., and even return to SNL to host almost ten years after his firing. He's come a long way from his discontented time on the show, and like many of his siblings he's passed on the Wayans comedy bug to the next generation; his son Damon Wayans Jr. has already appeared on several of his father's shows as well as New Girl and Happy Endings.

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